Antagonists of human CCR5 receptor containing 4-(pyrazolyl)piperidine side chains. Part 3: SAR studies on the benzylpyrazole segment

Bioorg Med Chem Lett. 2004 Feb 23;14(4):947-52. doi: 10.1016/j.bmcl.2003.12.006.

Abstract

Extensive SAR studies in our benzylpyrazole series of CCR5 antagonists have shown that both lipophilic and hydrophilic substituents on the phenyl of the benzyl group increase antiviral potency. However, improvements in pharmacokinetic profiles were generally only observed with more lipophilic substitutions. 4-Biphenyl (51) performed the best in this regard. Highly lipophilic substituents impart undesirable ion channel activity to these CCR5 antagonists. Alkoxy substituents provide a good balance of antiviral activity, pharmacokinetic parameters, and selectivity. Compounds 42b and 42d, containing a 3,4-dimethoxy substituent, are considered the most promising improvements over parent compounds 9. They demonstrate improved antiviral activity while retaining good pharmacokinetic profile and selectivity.

MeSH terms

  • Animals
  • Anti-HIV Agents / chemical synthesis
  • Anti-HIV Agents / chemistry*
  • Anti-HIV Agents / pharmacokinetics*
  • Biological Availability
  • CCR5 Receptor Antagonists*
  • Dogs
  • HeLa Cells
  • Humans
  • Molecular Structure
  • Monocytes / drug effects
  • Piperidines / chemical synthesis
  • Piperidines / chemistry*
  • Piperidines / pharmacokinetics*
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacokinetics
  • Rats
  • Structure-Activity Relationship

Substances

  • Anti-HIV Agents
  • CCR5 Receptor Antagonists
  • Piperidines
  • Pyrazoles